Methanol → 4-Methyl-pyridin 3-(4-methyl-thieno[3,2-c]pyridin-2-yl)-imidazolidin-2-one

HRID 80260

반응식

HRID 80260 반응식
[C:1](=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:13]2[CH:14]=[C:15]([N:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][C:27]=4[CH3:28])[C:18]3=[O:29])[S:16][C:12]=2[CH:11]=[CH:10][N:9]=1.CB(O)O.CO>C(Cl)(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:28][C:27]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.[CH3:1][C:8]1[C:13]2[CH:14]=[C:15]([N:17]3[CH2:21][CH2:20][NH:19][C:18]3=[O:29])[S:16][C:12]=2[CH:11]=[CH:10][N:9]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 498718701-(4-Chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

생성물 1

HCID 866494024-Methyl-pyridin 3-(4-methyl-thieno[3,2-c]pyridin-2-yl)-imidazolidin-2-one수율 16.39%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6212Chloroform용매

실험 절차

Tetrakis (triphenylphosphine) palladium (33 mg, 0.0288 mmol) was added to potassium carbonate (120 mg, 0.8649 mmol) previously purged with argon (30 minutes). The reaction mixture was purged with argon for 15 minutes, followed by the addition of 1-(4-chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (98A: 100 mg, 0.2883 mmol) and methyl boronic acid (21 mg, 0.3459 mmol). The reaction mixture was heated to reflux for 6 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated to afford the crude product. Purification by column chromatography on silica gel (3-4% MeOH in CHCl3), followed by preparative HPLC afforded 10 mg of the product (16.39% yield).

후처리

  1. custompreviously purged with argon (30 minutes)
  2. customThe reaction mixture was purged with argon for 15 minutes
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 6 hours
  5. concentrationThe reaction mixture was concentrated
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (3-4% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-3712b84dc51a459bada732b0799aa2ca
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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